1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(S_S)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol

Base Information

• Chemical Name: 1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(S_S)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol
• CAS No.: 678156-14-4
• Molecular Formula: C₂₂H₂₈O₄S
• Molecular Weight: 388.528
• Mol file: 678156-14-4.mol

Synonyms:1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(S_S)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol

Chemical Property of 1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(S_S)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(S_S)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol

There total 8 articles about 1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(S_S)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

8-benzyloxy-4-bromo-1-(SS)-(4-methylphenylsulfinyl)-(2R,3R,4S)-octane-2,3-diol (678156-04-2) → 1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(SS)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol (678156-14-4)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃; for 1.75h;

DOI:10.1016/j.tetasy.2003.12.017

Reference yield:

1 ,5-pentanediol (111-29-5) → 1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(SS)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol (678156-14-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 80 percent / NaH

2.1: 80 percent / PCC

3.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 70 percent / tetrahydrofuran; hexane / 3 h / -78 °C

4.1: 91 percent / ZnCl₂; DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 °C

5.1: 85 percent / H₂O; N-bromosuccinimide / toluene / 0.25 h / 20 °C

6.1: 83 percent / K₂CO₃ / methanol / 1.75 h / 0 - 20 °C

With N-Bromosuccinimide; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; pyridinium chlorochromate; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; toluene;

DOI:10.1016/j.tetasy.2003.12.017

Reference yield:

5-(benzyloxy)-1-pentanol (4541-15-5) → 1-[(3R)-(4-benzyloxybutyl)-(2R)-oxiranyl]-2-(SS)-(4-methylphenylsulfinyl)-(1R)-ethan-1-ol (678156-14-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / PCC

2.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 70 percent / tetrahydrofuran; hexane / 3 h / -78 °C

3.1: 91 percent / ZnCl₂; DIBAL-H / tetrahydrofuran; toluene / 0.67 h / -78 °C

4.1: 85 percent / H₂O; N-bromosuccinimide / toluene / 0.25 h / 20 °C

5.1: 83 percent / K₂CO₃ / methanol / 1.75 h / 0 - 20 °C

With N-Bromosuccinimide; water; diisobutylaluminium hydride; potassium carbonate; pyridinium chlorochromate; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; toluene;

DOI:10.1016/j.tetasy.2003.12.017

upstream raw materials:

8-benzyloxy-4-bromo-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3R,4S)-octane-2,3-diol

1 ,5-pentanediol

5-(benzyloxy)-1-pentanol

5-benzyloxy-1-pentanal

Downstream raw materials:

4-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-5-(S_S)-(4-methylphenylsulfinylmethyl)-(4S,5R)-1,3-dioxolane

5-[1-azido-5-benzyloxy-(1S)-pentyl]-2,2-dimethyl-(4S,5S)-1,3-dioxolan-4-ylmethanol

(+)-lentiginosine

4-azido-8-benzyloxy-1-(S_S)-(4-methylphenylsulfinyl)-(2R,3S,4S)-octane-2,3-diol